


Comedy Collaboration

by DRHPaints



Category: Conan O’Brien, Conan O’Brien RPF, John Mulaney - Fandom, John Mulaney RPF, Late Night Host RPF, US Comedians RPF
Genre: Blow Jobs, Explicit Language, Explicit Sexual Content, Marijuana, Multi, One Shot, Oral Sex, Smut, Threesome, Threesome - F/M/M, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2020-10-11
Updated: 2020-10-11
Packaged: 2021-03-07 17:00:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,096
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26941039
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: John Mulaney brings his girlfriend Laura along with him to his interview on 'Conan.' After filming wraps, the three of them hang out in the studio getting high, John and Laura confessing that they find Conan incredibly sexy. Flattered, Conan decides to take them up on it.
Relationships: Conan O’Brien/John Mulaney/Original Female Character
Kudos: 7





	Comedy Collaboration

**Author's Note:**

> Requested by mentallyelite on tumblr. Hope you enjoy!

Driving to the Burbank studio with Laura in the passenger seat, John found his long hands gripping the steering wheel and a wide grin crinkling his cheeks. He loved whenever he was invited onto Conan’s show. Even after all these years of performing his sets and doing interviews, John still couldn’t fathom that Conan considered him a friend after growing up and admiring the ginger comedy god’s talents on screen.

When Sona called to see if John was willing to come on to promote his newest album, John asked if Laura could tag along and thankfully it was no problem. To say Laura was a fan of Conan’s was putting it mildly. It was a few months into their relationship before John recognized a curious trend.

A devoted admirer himself, John watched Conan whenever he could, and he and Laura would often record his shows to view later if John was off doing sets or they were out at an event. But after a while, evenings spent curled up on the couch and laughing at Conan’s quirky antics, John noticed that Laura was particularly...affectionate afterward. 

Their sex life was consistently enjoyable, but after observing Conan, it was as if an extra log were tossed on the fire for Laura. She would paw at John, hands and mouth insistent and greedy as she dragged him to the bedroom, and John would smirk as she quivered beneath him, eyes closed, wondering if perhaps it wasn’t an orange pompadour she imagined hovering over her instead.

But he never thought it was worth calling her on. Until one night an episode of _Conan Without Borders_ aired. Arm around Laura on the couch, she began squirming next to him as a shirtless Conan in leather shorts fell under the ministrations of a dominatrix.

Eyes wide at the screen, Laura’s hand hastily tugged down the waist of his pajama bottoms, unearthing his soft cock. 

“Whoa...what’re you doing there?” John chuckled, raising an eyebrow at her.

Not taking her gaze from the television, Laura lowered her head. “I just...I need to suck you, John. _Now_.”

Gobbling his cock like she was dependent on it for life support, John massaged her scalp and writhed on the couch, fighting to keep his hips flat on the cushion. 

It was then he caught something curious about himself. For a while he watched Laura, the image of the warm circle of her mouth gliding up and down his long cock tantalizing, but then his cerulean eyes rose to Conan. John’s cock throbbed. At first he thought it was perhaps due to a movement of Laura’s throat, or a squeeze of her fingers, but staring at him, Conan’s tongue darted over his lips in his constant habit and John’s cock eagerly twitched again.

Well aware he wasn’t straight, John was still a bit unnerved that his longtime hero provoked this kind of response. But as Laura worked away, he found his mind spun endless scenarios. Conan’s large, freckled hands running over his skin. Burying his lengthy fingers in that fluffy ginger hair. Dropping to his knees before those slender hips.

Toes curling and cumming hard in the back of her throat, John emitted a closed-mouthed moan as he bit his lip in an effort not to say Conan’s name. It wasn’t that he was ashamed, per se, he mostly felt silly and that maybe what he and Laura were doing was a bit odd. 

But the next night, Conan didn’t even make it past the monologue before John brushed his lips over Laura’s neck, his hand creeping below the waistband of her panties. Laura rode his cock, both of them facing the television and panting hard, neither acknowledging the fact that their frantic humping slowed during commercial breaks.

Finally, after Conan waved goodbye and they collapsed on the couch in a pile of useless sweaty limbs, John combed back Laura’s hair. “Hey, so…” Folding his top lip under, John’s teeth held it for a moment. “Conan really turns you on, huh?”

Lifting a shoulder, Laura looked away, and were her skin not flushed from their lovemaking her cheeks would’ve reddened. “Yeah...sorry.”

“No.” John shook his head, giving her hip a squeeze. “Me...me too.”

“Really?” Laura raised an eyebrow.

Sheepish smile playing over his soft mouth, John tipped his head from side to side. “Yeah...I...I guess I think he’s pretty...sexy.”

Clapping her hands together excitedly, Laura swooped down to give John a kiss. “Yay! Oh that makes me feel so much better.” Laura leaned against John and sighed, bringing a hand to her chest. “I was so worried you’d be, you know...jealous or whatever if I said anything.”

“Nope.” Kissing her cheek, John shook his head. “I totally get it.”

Biting her lip, Laura carded her fingers through John’s brunette locks. “You know what would be really hot?”

“Hmm?” Smiling, John’s narrow hand slid down to pat her ass. 

“If I could have….” Laura polished John’s prominent cheekbone. “Both of you.”

“Ooh.” Closing his eyes, John nodded heavily. “ _Yes.”_

They discussed the possibilities, scenarios, and positions. And before John knew it he was hard again, he and Laura going at it for round two, but not before calling up Conan on the DVR to join them in the background.

So when they arrived John felt a bit awkward as he and Laura waited in the green room for Conan to greet them. A knock sounded at the door and John sat up, smoothing over the gray jacket of his suit. “Come in.”

Conan’s tall form appeared, raising a sizable hand in a wave. “Hey there.”

Standing, they embraced and John inhaled Conan’s delicious scent. A mix of bergamot and citrus and something else he couldn’t quite identify. “Hey buddy, this is my girlfriend, Laura.”

Gesturing to her, Laura wiggled her fingers nervously in the air. Strung wire tight in anticipation, finally meeting Conan face to face was daunting. She knew Conan was 6’4”, but confronting his height in person was another matter entirely. The Irish giant positively towered over her as his crystalline eyes locked into her own and he extended a huge palm. “Hey Laura, nice to meet you.”

“You too.” She hoped her voice sounded some semblance of natural as she shook Conan’s hand, finding it difficult to meet his piercing gaze. Laura pulled up the sleeve of her red dress. Taking extra care with her appearance, for a moment she thought she saw Conan’s baby blue eyes trailing over her cleavage, but wrote it off as her imagination as the three of them chatted before heading out to the studio.

John’s comedy brain kept serving up the most ridiculously inappropriate ideas for him to bat at Conan as they spoke. _Hey, thanks for making my girlfriend cum so hard. We go at it like crazy while you make jokes and dance around like a clown. Can’t stop thinking about how badly I want to suck your cock, man._ Smirking to himself, John sat in the chair across from Conan and they launched into the interview.

Observing from the front row of the audience, Laura beamed at the chemistry between the two handsome, hilarious men as they bantered and laughed. As per usual, she adored John in his crisp, dark grey suit, tie emblazoned with a tiny embroidered bee. Conan looked especially foxy in black skinny jeans and a black denim jacket over a gray button up with a black tie, and though Laura loved him in a suit as well, she found herself grateful for his new casual format, not for the first time.

After the shared mirth they wrapped and the three of them moseyed backstage, hanging out in the green room and talking, losing all track of time as they cracked one another up and reminisced about their shared experience at _SNL_ and doing live performances. 

Slapping his hands on his lean thighs, Conan stood. “Well, I’m thirsty. Do you guys want anything?”

“Sure.” John nodded and Laura did the same.

Conan gestured with two lengthy fingers. “Okay. Come on.”

Trying to keep up with his extended strides, they followed Conan down the hallway to the break room. Unlike when they entered, the floor was now almost eerily silent, lights extinguished and no longer abuzz with employees flitting to and fro. They each grabbed a water out of the fridge and, cracking them open, Conan leaned on the counter and tossed back about half of the bottle before shaking out his sleeve and looking at his watch.

“Hey, do you guys need to be anywhere?”

Eyes meeting, John and Laura shrugged. “No.” John shook his head. “Why?”

A devilish smirk played over Conan’s thin lips. “So, uh…” He scratched the back of his freckled neck. “Sona. She gave me some weed. She’s always trying to get me high to calm down.” Rolling his eyes, Conan held up a palm in exasperation. “But I really haven’t wanted to do it alone. I don’t have a lot of experience with pot. I’d feel better, you know…” Shrugging, Conan offered a half grin. “If I was around people I trust.”

“Oh.” Pulling his head back in surprise, John blinked. Then he turned to Laura and raised an eyebrow. “Well...what do you think?”

A smile blossomed over Laura’s plump lips. “Yeah. Sounds fun.”

“Okay.” John nodded in agreement. “Sure.”

Sighing, Conan bobbed his head. “Great, it’s just in my office.” 

Leading the way, once again Laura nearly had to jog to stay in step with Conan and John before he reached the door and unlocked it. Rifling in his desk, Conan emerged with a beautiful silver cigarette case and a lighter. “Come on, we can go hang out in one of the conference rooms.”

Conan locked his office and was opening the case to show them a dozen neatly rolled joints when they heard a throat clearing behind them. Spinning around they saw the cold eyes of Jordan Schlansky staring, his gaze traveling to the joints and then to each of their faces.

“Oh hey, Jordan.” Smiling, Conan tried to discreetly slide the case into his pocket, but it was too late.

Flat toned and arms crossed, Jordan gave him a hard look. “Conan, you’re here...late.”

Shrugging, Conan kept his tone light. “Yeah, we’re just hanging out.”

Jordan blinked for the first time since they encountered him and Laura was amazed at how animatronic he truly seemed. “Do you think that’s…” Eyes drifting once more toward where Conan stashed the weed, Jordan narrowed his eyes. “ _Wise?_ ”

Tilting his head, the corner of Conan’s mouth ticked up. “Hey Jordan. What’s the name of the show? Is it called ‘ _Jordan’?”_

Nose flaring a little, Jordan gave the briefest of head shakes. “No. It’s the _‘Conan’_ show.”

Conan just nodded. “And what time did you get here today?”

“I don’t see how that’s releva—“

“What time, Jordan?” Crossing his arms, Conan grinned.

Voice lowering a bit, Jordan shifted his weight uncomfortably. “I believe it was sometime after noon…”

“It was _one thirty in the fucking afternoon,_ Jordan.” Conan rocked forward onto his toes, shaking his head. “So until you get to work at a decent hour, and until your name is on the paychecks, maybe don’t tell me how I can spend my time in my own office.”

Conan’s tone was somewhat playful, but with a rod of steel beneath it. Jordan nodded. “Right. Well,” Again, his head turned between the three of them like he was a robot scanning for defects. “Have a good night, then.”

Conan chuckling, they proceeded down the hall and into the conference room. Aside from a few papers strewn on the desk and a whiteboard with half-completed joke ideas that didn’t remotely make sense out of context, it was empty and Conan opened the windows before they chose three chairs and sat down. 

Selecting one of the joints, Conan placed it between his thin lips and lit it, inhaling and coughing immediately. “Oh shit.” He blinked, handing it to John. “Obviously you can tell I don’t do this often.”

Accepting, John took a hefty puff of the sweet smoke and managed to hold it in as he passed off to Laura. They continued until the room was foggy and their eyes were red, Conan loosening his tie in the amiable silence.

Laura raised a hand to her brow. “Whoa...okay. I think it’s kicking in now.” The familiar heady sensation and lightness washed over her body and Laura blinked, taking in her surroundings.

“Yeah…” Nodding slowly, John swallowed. “Yeah, I think so.” Turning to Conan, John raised an eyebrow. “Are you feeling it?”

Conan dragged a big hand down his face. “Yeah, I am.” He smiled, eyes crinkling. “Wow, it’s strange. I haven’t smoked in such a long time. It’s strong stuff. The high is...different.” Furrowing his brow, Conan patted his chest. “More in the body kind of, right?” John nodded in understanding. 

“It makes sex fantastic.” Laura blurted out. Immediately her mouth dropped open in horror and she raised a hand to cover her face, but John and Conan just laughed. And found they couldn’t stop laughing. Laura joined in and soon the three of them were rolling with mirth, eyes watering as they fought to recover.

“I…” Chuckles squeaking out, Conan wiped away his tears. “I don’t know why that was so funny.”

Holding up his palms in defeat, John shook his head. “Me neither, but…” He pointed at Laura. “I bet you’re not wrong.”

“Huh.” Shifting his sharp jaw to the side, Conan blinked. “I’ve never had sex while high.”

“Ugh.” Allowing her head to flop back over her chair, Laura let out a deep sigh. “It’s great. Just...just a little more aware of everything, you know?”

“Oh yeah?” John twisted and untwisted the bottle cap on his water. “I’ve never done it either.” Watching Laura sit up and cross her shapely legs, a smirk grew on John’s lips and he decided to take a risk. “Hey Laura…” Tilting his head at Conan, he lifting his eyebrows. “You should tell him about that fantasy of yours.”

Eyes going wide, Laura gripped the sides of her chair and shook her head as Conan bent forward, placing an elbow on his knee and resting his chin on his fist. Conan launched into an old-timey Newspaper barker voice. “Oh, a fantasy, you say?” Laura couldn’t help but giggle despite her nerves. “Let’s hear all about it!”

“Well…” Hands crawling over themselves in her lap, she stared at the floor and could sense Conan and John’s eyes boring into her. “I kind of like the idea...I mean it could be hot…” Swallowing, Laura squirmed. “I just...think...both of you...would be sexy…” Voice fading practically to nothingness, Laura hung her head, chewing on the inside of her lip.

“Oh.” Conan sat back, corners of his mouth turned down appraisingly.

Rubbing her elbow with the opposite hand, Laura shook her head. “I’m sorry.”

Chuckling, Conan held up a hand. “Please. I’d rather gorgeous women _didn’t_ apologize for wanting to have sex with me.”

Sky blue eyes sliding over to John, Conan winced. “Oh. Sorry John.”

Waving a narrow hand, John smiled. “No, it’s fine. I’m well aware that she wants to climb you like some Irish weeping willow.”

Throwing back his head, Conan laughed and clutched his belly. Mouth opening in indignance, Laura pointed an accusatory finger at John. “Hey! No fair. You have to tell him, too.”

John froze as Conan eyed him. “Tell me what?”

Licking his lips, John adjusted himself in the chair and scratched his chin. “Well. I, um…” Clearing his throat, John wiped his hands on his slacks. “I guess...I guess I agree. With Laura. About...you know…” Looking away, John gave a little shrug.

Conan nodded slowly. “Wow. Alright. Huh.” Crossing his lanky legs at the ankle, he shook his head. “Strange. Do you know how much of my life I spent getting turned down? And now all of a sudden two beautiful people think I’m sexy for some crazy reason. Where were you in the 80s when Coney was so lonely?”

Giggling, Laura shook her head. “I don’t think you want us to answer that question honestly.”

Raising his almost impossibly faint orange eyebrows, Conan nodded. “Right. Reminding me I’m old. That’s the way to get me naked.” Gaze sliding in her direction, a smirk appeared on Conan’s lips as he retrieved the metal case from his pocket. “Want to do another?”

John eyed Conan, nodding. “Yeah. Sure.”

Sparking the joint, Conan inhaled, and as he held the smoke in his lungs he turned his eyes meaningfully to Laura, beckoning her with two long fingers. Cautiously she stood and walked toward him. Trying to hold his breath, Conan urged her forward faster, and Laura leaned down. Hooking a large freckled hand around the back of her neck, Conan drew her near, his thin lips meeting her own and opening her mouth with gentle pressure.

Lungs flooding with smoke as Conan exhaled into her, tendrils crept from their joined faces as Conan’s tongue briefly swept past her own before he retracted, caressing her cheek and smiling as she stood, exhaling and blinking in surprise.

Taking another drag as his gaze traveled up her body, Conan shifted his eyes. “John.” He called him over, voice froggy as he spoke while holding the hit in. John timidly rose from his chair and bent down before him. Joining Conan’s lips, nearly all the smoke was lost as John eagerly twisted their tongues together, unable to resist winding his fingers into Conan’s ginger locks. 

Not leaving John’s oceanic eyes, Conan passed the joint to Laura. Drawing the acrid smoke deep into her lungs, she watched as John and Conan kissed, John gradually straddling Conan in his chair as Conan’s massive hands came to knead his rounded hips.

Exhaling, Laura tapped John on the shoulder and he parted from Conan’s mouth with a puckering sound. She handed off the joint and captured Conan’s slender lips as John finished it with a deep puff, unbuttoning Conan’s shirt as she bent over him. 

John stood and shucked off his jacket, removing his tie as Laura tossed her leg over Conan’s lap, hurriedly removing his shirt as he kneaded her thighs and bunched her skirt up about her waist. Joining them, John pulled Laura’s hair aside to kiss her neck, fingers dipping into the cup of her bra to massage her breast as he leaned over their joined bodies seated on the chair.

Laura ground herself into the growing erection evident through Conan’s jeans and he rocked his hips forward into her warmth. After a couple minutes drinking deep of one another’s mouths, Conan parted, panting. “Should we get on the floor?”

Laura nodded enthusiastically, climbing off. Conan double checked to make sure the door was locked before pulling his undershirt overhead and letting it flutter to the ground. The three of them disrobed rapidly before kneeling together on the carpet. John linked to Laura’s lips, caressing her breast, other hand flowing down to spread her open and begin circling her clit with aching precision. Conan scooted in behind her, strong hands massaging her shoulders before tossing aside her hair to brush his thin lips over her neck. Nipping at her ear and dragging his teeth over her sensitive skin, Conan lowered himself and began gliding his stiff cock into the crack of her ass, pushing Laura fervently into John’s fiddling fingers.

Moaning, Laura fought to keep her mouth moving against John, but failed as her hand cascaded over his skinny frame, grasping his cock and tugging wildly. Eyes falling shut in rapture, John rocked forward into the warm circle of her fist, mewls of delight rising in his thin chest. Grabbing two handfuls of her ass and thrusting hard, Conan bit down on her neck, growling, before he paused and straightened up. “Fuck.” Blinking, Conan looked around. “I don’t have a condom.”

Pointing insistently at her chair, Laura nodded. “My purse. Pretty sure I have one.”

Conan hopped up to retrieve it, rifling through the varied contents until he found the tiny package, holding it aloft in triumph before getting back on his knees behind her.

John working her clit, Laura’s hand clung to his shoulder as she started to quake. Reaching an arm underneath, two of Conan’s extended fingers dipped inside of her as he brought his lips to her ear, breath hot and urgent. “Do you want me to fuck you, Laura?”

“Yes.” Laura gasped, spreading her legs to force Conan’s digits deeper inside. “Fuck me, Conan. Please”

A deep chuckle rumbling up from his chest, Conan rolled the condom over himself. Positioning her hips, John removed his hand and Conan surged inside of her, swiveling to ensconce himself fully in Laura’s warm grip.

Laura’s back arched as Conan’s thick cock stretched her open and she went down on her hands, patting John’s hip. “Come on. Let me suck you.”

“Okay.” Nodding, John scooted to the side until his substantial cock hung heavy and purple before Laura’s waiting lips. Taking him into her mouth, Conan’s first pounding stroke drove her forward and the head of John’s cock buried itself in the back of her throat.

“Oh Laura, _yesss!”_ John hissed appreciatively, fingers weaving into her hair as she hollowed her cheeks and sucked. Conan hooked an arm around her hip, fingers racing over Laura’s clit. As he pummeled forth, high noises of ecstasy muffled by John’s cock rose in Laura’s throat and she flickered around Conan’s sensitive flesh.

Laura adored having sex with John. He was generous and thoughtful and she never left their lovemaking unsatisfied. But that’s exactly what it was: lovemaking. John was a tender, considerate man and he worshipped her body, cherishing Laura dearly. 

But sometimes a woman just needs to get _fucked._ And Conan was more than happy to provide as he hammered into her with his massive cock, wide palm of his free hand cracking across her round ass as he gritted his teeth, every muscle in his sharp jaw popping. 

Screaming and overwhelmed, Laura allowed John’s cock to drop from her mouth, jerking vigorously as she constricted around Conan, body shaking and fingers digging into the carpet.

“Mmm...fuck yeah, cum on my cock.” Conan uttered, a smile in his voice as he continued to clap against her ass, relentless. Recovering slightly, Laura managed to devour John once more, taking him down to the root and firmly pressing her tongue to the underside of his cock, fondling his balls and pulling a little in the way she knew drove John mad.

Whimpering, John curled over her prone form. “ _Oh Laura! Yes! Your mouth! I love it!”_ Eyes clenched tight, John’s hands were braced on Laura’s back and Conan saw the look of desirous anguish on his face. Finding it insatiably erotic, Conan clasped John’s carved cheek, snatching him close and mashing their lips together. Tongues dancing, Conan slammed into Laura, every upstroke shoving John’s cock into the moist recesses of her throat as he furiously twiddled her clit. 

Breaking away, Conan rested his forehead to John’s. “Fuck, John. You’re so goddamn pretty.” He gasped, sensing Laura tighten about him again.

Hand scrambling at Conan’s shoulder, the other gripped Laura’s scalp as John whined. “ _Yes! Laura! Conan! Don’t stop! Fuck! FUCK!”_

For a moment they were nothing other than a mass of pulsing, panting limbs until the storm broke, John crumbling first, painting the back of Laura’s throat with hot, salty cum as he shivered and frantically groped for the seat of a chair to stay aloft. Followed by Laura, forehead falling to the floor and sticky white liquid dripping from her mouth as she screamed and seized around Conan’s cock, eyes rolling. Lastly, the intense pressure from Laura’s body leading him off the cliff, Conan’s hips juddered forward, mouth agape in a stuttered, moaning whimper with his eyes clasped shut before he settled back on his heels, gulping air.

Dislodging themselves, the three of them tried to catch their breath on the floor of the conference room, pushing sweaty hair out of their faces and looking around.

“Well…” Conan glanced at the two of them, smirking and crossing his gangly legs. “Thanks for coming on the show. This was a lot of fun.”

John laughed, nodding. “Yeah.” He looked between Laura and Conan. “Not exactly the type of performance I was expecting to give.”

**Author's Note:**

> Thank you for taking the time to read! If you enjoyed this story, please leave a comment or come say hi on tumblr at fandomtransmandom. I also take requests!


End file.
